Towards the synthesis of the ABC tricycle of Taxol
Towards the synthesis of the ABC tricycle of Taxol
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发表时间：
2015
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通讯作者：
Antonia Wilkes
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作者：
Antonia Wilkes
紫杉醇是世界上治疗癌症最成功的药物之一。从太平洋红豆杉(Taxus Brevifolia)的树皮中分离出来，是有机化学中非常感兴趣的分子；自发现以来，已进行了六次合成和许多合成工作。计划对Holton合成中的中间体进行半收敛合成。总体合成计划如下所示。A环将通过分子内频那醇缩合来安装。BC自行车将在C10-C11通过闭合化合关闭。C12位的酮将被保护为炔，而BC自行车前驱体将通过偶联片段A和C环而得到。本论文描述了模型C环的制备，它没有C7上的含氧官能团，与碎片A一起被成功地合成。我们合成了复分解前驱体并尝试了金的水合反应。
Taxol is one of the world’s most successful drugs used in the treatment of cancers. Isolated from the bark of the Pacific yew tree (Taxus brevifolia), it is a molecule of great interest within organic chemistry; with six total syntheses and a number of synthetic works having been published since its discovery. A semi-convergent synthesis of an intermediate in Holton’s synthesis was planned. The overall synthetic plan is shown below. The A ring would be installed by an intramolecular pinacol condensation. The BC bicycle would be closed by ring-closing metathesis at C10-C11. The ketone at C12 would be protected as an alkyne and the BC bicycle precursor would be obtained by coupling fragment A and the C ring. This thesis describes the preparation of a model C ring, without the oxygenated functionality at C7, was successfully synthesised along with fragment A. Metathesis precursors were synthesised and gold hydration reactions were attempted.